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2020-02-21

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cc-by-nc (c) ARKAT-USA, 2020
Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/159496

Preparation of tetrahydro-1H-xanthen-1-one and chromen-1-one derivatives via a Morita-Baylis-Hillman/oxa-Michael/elimination cascade

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https://doi.org/10.24820/ark.5550190.p011.133

Abstract

The Morita-Baylis-Hillman (MBH) reaction is a carbon-carbon bond forming transformation between an electrophile, typically an aldehyde, and an activated olefin. MBH adducts obtained from 2-hydroxy- benzaldehydes and cyclic enones are potential substrates for the synthesis of xanthenone and chromenone derivatives. In this work, we investigated conditions to obtain tetrahydro-1H-xanthen-1-ones and chromen- 1-ones directly via a Morita-Baylis-Hillman/oxa-Michael/elimination cascade catalyzed by a bifunctional, bicyclic imidazolyl alcohol (BIA), which proved to be an effective catalyst for this transformation. The reactions were performed at room temperature in water to give the products in 10-74 % yield.

Subject

Catàlisi, Imidazoles, Química de l'aigua

Subject (English)

Catalysis, Imidazoles, Water chemistry

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Articles publicats en revistes (Química Inorgànica i Orgànica)

Citation

RODRIGUES, Jr., et al. Preparation of tetrahydro-1H-xanthen-1-one and chromen-1-one derivatives via a Morita-Baylis-Hillman/oxa-Michael/elimination cascade. Arkivoc. 2020. Vol. 2020, num. part ii, pags. 77-88. ISSN 1551-7012. [consulted: 19 of August of 2026]. Available at: https://hdl.handle.net/2445/159496

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